It really depends on how the housing market is where you are. Unfortunately right now in many areas the market is a seller's market. This is because the interest rates are very low right now (under 7% in many cases!) and so there are more buyers than sellers in many areas.
Where I live in Fairfax, VA, prices have gone up like crazy on homes. They have been going so crazy that many people have been purchasing homes above what their assessments are coming in at. (A townhouse last summer that was selling for $230,000 is now selling for $285,000-300,000 ... They're nice homes, but that is a HUGE increase in price for only 1 year, an almost 25% increase in price in 1 year ... way better than the stock market right now). Prices in this area tend to go for above list price, however, in your area it may be different.
It really comes down to whether or not you really want the house. In the long term, an extra $5,000 really isn't a lot of money if you intend to stay in the house for many years. Thats the way I started to rationalize things when I made a few offers on homes at under list price or at list price and was getting beaten by people offering more. Remember if the market is hot and the seller gets more than 1 bid than the ball is really in the seller's court. He or she has the advantage at that point, and if you really want this house a lowball offer could easily make you lose the house. (In my experience, most people do not play the bidding war game and hope you'll increase your price... At least not in this area).
Good luck with the house hunting! It took me over 3 months to find something that I was able to afford, able to live in, and able to purchase at list price ... but I finally did (after writing 4 other losing contracts!!!)
EDIT:
BTW- In terms of a buyer's agent, it depends on where you live, but in VA and NJ the general way things work is like this: 6% fee; 1.5% to selling agent, 1.5% to selling agent's company, 1.5% to buyer's agent, 1.5% to selling agent's company (adds up to the 6% fee that the seller generally pays).
A good buyer's agent will realize that if they get you a good deal and treat you right that you will most likely recommend them to your friends and most likely use them as your selling agent when you decide to sell and "upgrade" (that is common practice in the area where I live). If you offer 7% less and get it, you're talking a loss of $367.50 to the buying agent ... Not a huge loss. There *are* buyer's agents out there that are just looking to make a quick sale, and at as much money as possible. But before you start house hunting, you should search for a buyer's agent that you are comfortable with. My buyer's agent agreed to not force me to sign an exclusivity clause with her until after she proved to me that she would do the job right for me. And for 2 months she showed me countless homes, when I could have easily bought a house without her and she would have gotten nothing. Of course, I would never do that and I signed a contract with her when I wrote the first contract on my house. But she always was willing to help me do the market research and even tell me outright when a house was too expensive or not worth the list price. I've found for the most part that agents that are out to make a quick buck want you to sign that contract with them right away where as agents who are dedicated want to prove to you that they're trustworthy before you sign the contract. Thats not 100% true of course, but from my experience thats the general trend I found. Anyways, if you dont already have a buyer's agent you should definitely try to find one. Another good thing to check out is that the buyer's agent doesnt only promote properties which their own company is selling or that they themselves are selling. This is a sneaky tactic that can hurt you as a buyer. My agent always called me when ANY property that matched my criteria came up, regardless of who was listing it.